115398-63-5

Basic information

• Product Name: 1-(3-Bromopropyl)-2-nitro-1H-imidazole
• Synonyms: 1-(3-Bromopropyl)-2-nitro-1H-imidazole;1-(3-bromopropyl)-2-nitroimidazole
• CAS NO: 115398-63-5
• Molecular Formula: C₆H₈BrN₃O₂
• Molecular Weight: 234.05062
• Mol File: 115398-63-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(3-Bromopropyl)-2-nitro-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-Bromopropyl)-2-nitro-1H-imidazole(115398-63-5)
• EPA Substance Registry System: 1-(3-Bromopropyl)-2-nitro-1H-imidazole(115398-63-5)

Safety Data

• Hazardous Substances Data: 115398-63-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(3-Bromopropyl)-2-nitro-1H-imidazole is used as an active pharmaceutical ingredient for its antimicrobial and antiprotozoal properties, targeting the growth of certain microorganisms and contributing to the development of treatments for bacterial and parasitic infections.
Used in Drug Development:
1-(3-Bromopropyl)-2-nitro-1H-imidazole is used as a key component in the development of new drugs, particularly those aimed at treating infections. Its ability to selectively target and inhibit the growth of specific microorganisms makes it a promising candidate for the creation of more effective and targeted treatments.
Used in Organic Chemistry Research:
1-(3-Bromopropyl)-2-nitro-1H-imidazole is utilized as a versatile compound in organic chemistry due to its potential for further functionalization and modification. This allows researchers to explore new chemical reactions and synthesis processes, potentially leading to the discovery of novel compounds with various applications.
Used in Drug Discovery Research:
1-(3-Bromopropyl)-2-nitro-1H-imidazole is employed in drug discovery research to identify new therapeutic targets and develop innovative treatments for various diseases. Its unique chemical structure and properties make it a valuable tool in the search for new drugs and therapies.

Upstream product

• 527-73-1 2-nitro-1H-imidazole 
• 109-70-6 1.3-chlorobromopropane 
• 109-64-8 1,3-dibromo-propane 

Downstream Products

• 1214889-84-5 N-[3-(3-fluoro-4-{4-[3-(2-nitro-imidazol-1-yl)-propyl]-piperazin-1-yl}-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide 

Relevant articles and documents

Synthesis of Mitochondria-Anchored Nitroimidazoles with a Versatile NIR Fluorophore for Hypoxic Tumor-Targeting Imaging and Chemoradiotherapy

Nitroimidazoles are one of the most common radiosensitizers investigated to combat hypoxia-induced resistance to cancer radiotherapy. However, due to poor selectivity distinguishing cancer cells from normal cells, effective doses of radiosensitization are much closer to the doses of toxicity induced by nitroimidazoles, limiting their clinical application. In this work, a tumor-targeting near-infrared (NIR) cyanine dye (IR-808) was utilized as a targeting ligand and an NIR fluorophore tracer to chemically conjugate with different structures of hypoxia-affinic nitroimidazoles. One of the NIR fluorophore-conjugated nitroimidazoles (808-NM2) was identified to preferentially accumulate in hypoxic tumor cells, sensitively outline the tumor contour, and effectively inhibit tumor growth synergistically by chemotherapy and radiotherapy. More importantly, nitroimidazoles were successfully taken into cancer cell mitochondria via 808-NM2 conjugate to exert the synergistic effect of chemoradiotherapy. Regarding the important roles of mitochondria on cancer cell survival and metastasis under hypoxia, 808-NM2 may be hopeful to fight against hypoxic tumors.

Identification of novel 4-anilinoquinazoline derivatives as potent EGFR inhibitors both under normoxia and hypoxia

A novel series of 4-anilinoquinazoline derivatives (19a-19t) were designed and synthesized through incorporation of the 2-nitroimidazole moiety into the 4-anilinoquinazoline scaffold of EGFR inhibitors. The most promising compound 19h displayed potent EGF

Modulation of in vivo distribution through chelator: Synthesis and evaluation of a 2-nitroimidazole-dipicolylamine-99mTc(CO)3 complex for detecting tumor hypoxia

Previous studies have clearly demonstrated strong correlation between in vivo distribution and blood clearance of radiopharmaceuticals for the detection of hypoxia. Present study describes an attempt to improve the in vivo distribution of a previously reported 2-nitroimidazole-99mTc(CO)3 complex by tuning its blood clearance pattern through structural modification of the ligand. Herein, a 2-nitroimidazole-dipicolylamine ligand (2-nitroimidazole-DPA) was synthesized in a two-step procedure and radiolabeled with 99mTc(CO)3 core. Subsequently, the complex was evaluated in Swiss mice bearing fibrosarcoma tumor. As intended by its design, 2-nitroimidazole-DPA-99mTc(CO)3 complex was more lipophilic than previously reported 2-nitroimidazole-DETA-99mTc(CO)3 complex (DETA - diethylenetriamine) and showed slower blood clearance. Consequently it showed higher tumor uptake than 2-nitroimidazole-DETA-99mTc(CO)3 complex. Significantly, despite structural modifications, other parameters such as the tumor to blood ratio and tumor to muscle ratio of the 2-nitroimidazole-DPA-99mTc(CO)3 complex remained comparable to that of 2-nitroimidazole-DETA-99mTc(CO)3 complex. Present study demonstrates the feasibility of structural modifications for improving in vivo tumor uptake of hypoxia detecting radiopharmaceuticals. This might encourage researchers to improve suboptimal properties of a potential radiopharmaceuticals rather than ignoring it altogether.

Polyboron phenylalanine compound containing nitroimidazole, as well as preparation method and application thereof

The invention discloses a polyboron phenylalanine compound containing nitroimidazole as shown in a general formula (I) in the specification or pharmaceutically acceptable salt thereof, as well as a preparation method and application thereof. The compound

Tripterine imidazole derivative as well as preparation method and application thereof

The invention discloses a novel tripterine imidazole derivative as well as a preparation method and application thereof, and belongs to the field of biomedicine. The tripterine imidazole derivative has a structure shown as a formula I as shown in the specification, wherein R1, R2 and R3 are respectively selected from H, alkyl, hetero-atomic alkyl, halogen or nitryl; and X is selected from a saturated or unsaturated linear aliphatic hydrocarbon fragment containing 3-6 carbon atoms. The novel tripterine imidazole derivative as well as the preparation method and the application thereof disclosedby the invention have the benefits that the preparation method of the compound is mild in reaction conditions; a used reagent is low in toxicity, raw materials are easy to obtain, the post-treatment is convenient, and the yield is relatively high. Pharmacological experiment studies shows that the compound has excellent anti-tumor activity and can be applied to the preparation of an anti-tumor drug.

Design, synthesis and biological evaluation of 6-(nitroimidazole-1 H -alkyloxyl)-4-anilinoquinazolines as efficient EGFR inhibitors exerting cytotoxic effects both under normoxia and hypoxia

A series of novel 6-(nitroimidazole-1H-alkyloxyl)-4-anilinoquinazoline derivatives (15a-15r) were designed, synthesized and evaluated as efficient EGFR inhibitors through introduction of hypoxia activated nitroimidazole moiety into the quinazoline scaffold of EGFR inhibitors. The majority of these newly synthesized compounds exhibited comparable EGFR inhibitory activities to gefitinib and moderate to excellent anti-proliferative activities against HT-29 cells under normoxia and hypoxia. The most promising compound 15c displayed the IC50 value of 0.47 nM against EGFR kinase and excellent cytotoxic effect against HT-29 cells under normoxia and hypoxia with the IC50 values of 2.21 μM and 1.62 μM, respectively. The mimic reductive activation study revealed that compound 15c exerted reductive activation properties under hypoxia, which were consistent with the in vitro metabolic study, wherein 15c was easily reductive activated under hypoxia and much more stable under normoxia. All these results suggested that 15c was a potential cancer therapeutic agent both under normoxia and hypoxia and was worth of further development.

Syntheses of 2-nitroimidazole derivatives conjugated with 1,4,7-triazacyclononane- N, N ′-diacetic acid labeled with F-18 using an aluminum complex method for hypoxia imaging

Hypoxia imaging is important for diagnosis of ischemic diseases, and thus various 18F-labeled radiopharmaceuticals have been developed. However, 18F-labeling requires multistep procedures including azeotropic distillation, which is complicated and difficult to automate. Recently, 18F-labeling method using Al-F complex in aqueous solution was devised that offered a straightforward 18F-labeling procedure. We synthesized nitroimidazole derivatives conjugated with 1,4,7-triazacyclononane- 1,4-diacetic acid (NODA) that can be labeled with 18F using Al-F complex and examined their radiochemistries, in vitro and in vivo biological properties, and animal PET imaging characteristics. We found that the synthesized derivatives have excellent 18F-labeling efficiencies, high stabilities, specific uptakes in cultured hypoxic tumor cells, and high tumor to nontumor ratios in xenografted mice. Furthermore, the derivatives were labeled with 18F in a straightforward manner within 15 min at high labeling efficiencies and radiochemical purities. In conclusion, 18F-labeled NODA-nitroimidazole conjugates were developed and proved to be promising hypoxia PET agents.

Synthesis of nitroimidazole derived oxazolidinones as antibacterial agents

A series of N-alkylated derivatives of nitroimidazolyl oxazolidinones 6a-i with various substituent at N-1 position of the nitroimidazole were synthesized and their in-vitro antibacterial activities were evaluated against several Gram-positive and Gram-ne

An efficient procedure for the 1-alkylation of 2-nitroimidazoles and the synthesis of a probe for hypoxia in solid tumours

The N-alkylation of 2-nitroimidazole through its 'naked' anion, formed from its alkali metal salts in the presence of crown ethers and in homogeneous solution, is shown to be a useful preparative procedure. The reactions of α,ω-dihaloalkanes can be controlled to afford either the mono- or diheteroarylalkane. The procedure has been used to alkylate theophylline and to prepare a compound of use as a probe to identify, locate and quantify hypoxia in sections from solid tumours.